Cucurbitane-type triterpenoids from the branches and leaves of Elaeocarpus sylvestris

The chemical structures of nine cucurbitane-type triterpenoids from the branches and leaves of Elaeocarpus sylvestris (Elaeocarpaceae), including undescribed 29-hydroxymogroside I E₂, epimogroside I E₂, epimogroside I E₁, 24-oxomogroside I E₁, and 11-O-acetylmogroside I E₁, were determined using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. The absolute configuration of 29-hydroxymogroside I E₂ was confirmed by performing an X-ray diffraction analysis. Cucurbitacin D and 11-O-acetylmogroside I E₁ showed cytotoxicity toward human leukemia HL-60, human lung adenocarcinoma A549, human hepatoma SMMC-7721, human breast cancer MCF-7, and human colon cancer SW480 cell lines. The presence of a 11-O-acetyl group might increase the cytotoxicity of this type of triterpenoids.     

Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia

Five cucurbitacins, kuguacins A-E (1-5), together with three known analogues, 3beta,7beta,25-trihydroxycucurbita-5,(23E)-diene-19-al (6), 3beta,25-dihydroxy-5beta,19-epoxycucurbita-6,(23E)-diene (7), and momordicine I (8), were isolated from roots of Momordica charantia. Structures of 1-5 were elucidated by NMR and MS spectroscopic analysis. Among them, compounds 3-5 possess an unprecedented 25,26,27-trinorcucurbitane backbone. Compounds 3 and 5 showed moderate anti-HIV-1 activity with EC(50) values of 8.45 and 25.62 microg/ml, and exerted minimal cytotoxicity against C8166 cells (IC(50)>200 microg/ml), with a selectivity index more than 23.68 and 7.81, respectively.     

比色法测定苦瓜中的总皂甙

本试验通过对高氯酸和硫酸体系进行比较,选择香草醛-冰醋酸-高氯酸体系作为测定苦瓜皂甙的合适显色条件,并对体系中各个因素逐一考察,确定比色法测定苦瓜皂甙的条件为：0．2mL冰醋酸,0．8mL高氯酸,5％香草醛．冰醋酸溶液,70℃条件下反应20min。试验以苦瓜皂甙建立了苦瓜皂甙测定回归曲线,线性和稳定性可靠,平均加标回收率100．78％,变异系数为1．910％。     

苦瓜胚胎学研究

以石蜡制片法对苦瓜(Momordica charantia L.)进行了胚胎学研究。小孢子母细胞减数分裂时,胞质分裂为同时型,形成四面体型四分体和左右对称型四分体。成熟花粉为二细胞型。子房三室,双珠被,厚珠心,倒生胚珠。大孢子四分体为线形,合点端功能大孢子发育成为蓼型胚囊。中央细胞细胞质中有大量贮藏物质存在。极核在受精时融合。双受精过程属有丝分裂前配子融合类型。3个反足细胞随受精过程进行而退化。胚胎发生为柳叶菜型。核型胚乳,合点端具胚乳吸器。     

Hydroxyshengmanol-type triterpenoids from the aerial parts of Cimicifuga simplex Wormsk

New hydroxyshengmanol-type triterpenoids (1–8) were identified from the aerial parts of cimicifuga simplex Wormsk by comprehensive 1D and 2D NMR, MS, and single-crystal X-ray diffraction analyses. The absolute configuration of the himeketal carbon (C-16) in hydroxyshengmanol-type constituents from cimicifuga spp. was initially determined as R using X-ray diffraction. All compounds were evaluated for their cytotoxicity in a panel of cancer cell lines and acetylcholinesterase inhibitory activity.     

Cycloartane triterpenoids from the aerial parts of Cimicifuga foetida Linnaeus

Cycloartane triterpenoids, 2′,24-O-diacetylisodahurinol-3-O-α-l-arabinopyranoside, 24-O-acetylisodahurinol-3-O-α-l-arabinopyranoside, 12β-hydroxy-25-anhydrocimigenol, cimigenol-12-one, 12β-hydroxy-15-deoxycimigenol, 2′-O-acetyl-24-epi-cimigenol-3-O-α-l-arabinopyranoside, 2′-O-acetylcimigenol-3-O-β-d-xylopyranoside, 25-anhydrocimigenol-3-O-α-l-arabinopyranoside, 2′,23-O-diacetylshengmanol-3-O-α-l-arabinopyranoside, and 2′,24-O-diacetyl-25-anhydrohydroshengmanol-3-O-α-l-arabinopyranoside, together with eight known compounds, were isolated from aerial parts of Cimicifuga foetida. Their structures were determined by application of spectroscopic analyses and chemical methods. Biological evaluation of the compounds against human HL-60, SMMC-7721, A549, SK-BR-3, and PANC-1 cell lines indicated that three of these compounds exhibited broad-spectrum and moderate cytotoxic activities, with IC₅₀ values ranging from 6.20 to 22.74 μM. By comparing previous cytotoxic testing data and bioassay results from this study, preliminary structure–activity relationships of compounds with a cimigenol-skeleton can be proposed.     

苦瓜提取物的抑菌活性研究

本文研究了苦瓜(MC)不同活性成分的抑菌活性.结果表明:苦瓜提取物对细菌的抑菌作用明显,但对霉菌、酵母菌的抑制效果不明显.苦瓜粗皂甙和苦瓜粗多糖的抑菌效果比纯品的好.苦瓜乙醇浸提物、苦瓜粗多糖、苦瓜多糖、苦瓜粗皂甙、苦瓜皂甙、苦瓜粗蛋白对藤黄八叠球菌的最低抑菌浓度(MIC)分别为50、100、5、100、2、20 mg/mL.苦瓜多糖、苦瓜皂甙和苦瓜蛋白是苦瓜抑菌活性功能成分.     

Cucurbitane triterpenoids from the leaves of Momordica charantia, and their cancer chemopreventive effects and cytotoxicities

Seventeen cucurbitane-type triterpenoids, 1-17, including six new compounds, (23E)-3β,25-dihydroxy-7β-methoxycucurbita-5,23-dien-19-al (1), (23S*)-3β-hydroxy-7β,23-dimethoxycucurbita-5,24-dien-19-al (6), (23R*)-23-O-methylmomordicine IV (7), (25ξ)-26-hydroxymomordicoside L (8), 25-oxo-27-normomordicoside L (9), and 25-O-methylkaravilagenin D (12), were isolated from a MeOH extract of the leaves of Japanese Momordica charantia. The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Compounds 1-17 were examined for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced with 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, a known primary screening test for inhibitors of tumor promotion. Four compounds, 1, (23E)-3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al (2), karavilagenin D (11), and 12, showed potent inhibitory effects on EBV-EA induction with IC(50) values in the range of 242-264 mol ratio/32 pmol TPA. In addition, compounds 1 and 11 exhibited inhibitory effects on skin-tumor promotion in an in vivo two-stage mouse skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator, and with TPA as a promoter. Furthermore, upon evaluation of the cytotoxic activities of compounds 1-17 against human cancer cell lines, compounds 2, 5-7, 9, and 14 showed potent activities against HL60 cell line, and compound 2 against SK-BR-3 cell line.     

苦瓜降血糖活性部位的高通量筛选研究

PPAR与2型糖尿病存在密切关系,该受体已成为抗2型糖尿病的主要靶点。苦瓜是一种民间的中草药,药理实验文献报道具有显著的降血糖作用。本文以PPAR三种亚型PPARα、PPARγ,和PPARβ／δ为靶点的高通量筛选模型,对苦瓜多糖进行活性筛选。筛选结果表明MC-3对PPARδ和PPARγ具有较强的激活效果,其激活倍数分别达1．995、1．689。MC．3是一种潜在的降糖、降脂的活性部位。     

HPLC-ELSD测定苦瓜皂甙的含量

本文用HPLCELSD法测定苦瓜中皂甙B的含量。色谱条件:色谱柱ZorbaxSBC18,4.6×150mm;检测器ELSD(EvaporativeLightScatteringDetector);柱温30℃;流动相:甲醇水(70:30);流速1.0mL/min,N2压力:2.0×105Pa。皂甙B的保留时间在为7.295min,在浓度为0.1058～5.290μg/μL之间有很好的线性关系(R2=0.9918)。平均加标回收率为100.27%(n=3),RSD=2.83%。实验结果表明此方法可以作为苦瓜皂甙的定量测定方法     

Cucurbitane-type compounds from Momordica charantia: Isolation,in vitro antidiabetic,anti-inflammatory activities and in silico modeling approaches

Momordica charantia L., commonly known as bitter melon, belongs to the Cucurbitaceae family. Various in vitro and in vivo studies have indicated that extracts of bitter melons have anti-diabetic properties. However, very little is known about the specific purified compounds responsible for these antidiabetic properties. In the present study, 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al, charantal, charantoside XI, and 25ξ-isopropenylchole-5, 6-ene-3-O-d-glucopyranoside were isolated from bitter melon fruit. The structures of the purified compounds were elucidated by HR-ESIMS, 1D, and 2D NMR experiments. All compounds exhibited significant inhibition of α-amylase and α-glucosidase comparable to acarbose. Molecular docking studies demonstrated that purified compounds were able to bind to the active sites of proteins. Additionally, the purified compounds showed significant anti-inflammatory activity, downregulating the expression of NF-κB, iNOS, IL-6, IL-1β, TNF-α, and Cox-2 in lipopolysaccharide-activated macrophage RAW 264.7 cells. Our findings suggest that the purified compounds have potential anti-diabetic and anti-inflammatory activities and therefore hold promise for the development of plant-based management for diabetic and inflammatory conditions.     

Catalytic synthesis and antioxidant activity of sulfated polysaccharide from Momordica charantia L.

Sulfated derivatives of polysaccharide from Momordica charantia L. (MCPS) with different degree of sulfation (DS) were synthesized by chlorosulfonic acid method with ionic liquids as solvent. Fourier transform infrared spectra and ¹³C nuclear magnetic resonance spectra indicated that C‐6 substitution was predominant in MCPS compared with the C‐2 position. Compared with the native polysaccharide from Momordica charantia L. (MCP), MCPS exhibited more excellent antioxidant activities in vitro, which indicated that sulfated modification could enhance antioxidant activities of MCP. Furthermore, high DS and moderate molecular weight could improve the antioxidant activities of polysaccharide. © 2013 Wiley Periodicals, Inc. Biopolymers 101: 210–215, 2014.     

Pentacyclic triterpenoids from the aerial parts of Lantana camara and their nematicidal activity

Two new olean-12-ene triterpenoids, camarolic acid (1) and lantrigloylic acid (2), have been isolated from the aerial parts of Lantana camara, along with ten known triterpenes, namely, camaric acid, lantanolic acid, lantanilic acid, pomolic acid, camarinic acid, lantoic acid, camarin, lantacin, camarinin, and ursolic acid. The new compounds have been characterized as 3,25-epoxy-3alpha-hydroxy-22beta-{[(S)-3-hydroxy-2-methylidenebutanoyl]oxy}olean-12-en-28-oic acid (1) and 3,25-epoxy-3alpha-hydroxy-22beta-[(3-methylbut-2-enoyl)oxy]olea-9(11),12-dien-28-oic acid (2) through spectroscopic studies and a chemical transformation. Seven of the constituents, namely pomolic acid, lantanolic acid, lantoic acid, camarin, lantacin, camarinin, and ursolic acid, were tested for nematicidal activity against root-knot nematode Meloidogyne incognita. Pomolic acid, lantanolic acid, and lantoic acid showed 100% mortality at 1 mg/ml concentration after 24 h, while camarin, lantacin, camarinin, and ursolic acid exhibited 100% mortality at this concentration after 48 h. These results are comparable to those obtained with the conventional nematicide furadan (100% mortality at 1 mg/ml concentration after 24 h).     

长白大苦瓜高效再生系统的建立

目的:长白大苦瓜是蔬菜新品种,其高效再生系统的建立有助于蔬菜的快速生产,克服季节性、地域性对蔬菜生产的影响。方法:通过不同激素之间的配比寻找合适的种子萌发、不定芽分化和生根培养基。结果:预处理可有效提高种子萌发率,并获得长势整齐、健壮的无菌苗。添加6-BA 0.5mg/L NAA 0.5mg/L的培养基诱导的不定芽分化率较高,而激素组合6-BA 2mg/L NAA 0.5mg/L则对诱导丛生芽具有较好的效果。添加NAA 0.5mg/L能使试管苗的生根率达到50%。经过3d炼苗,移入腐叶土和泥炭土比例为1∶1的基质土壤中就可以正常生长。结论:长白大苦瓜可以建立高效的再生系统,实现试管苗的快速生产。     

苦瓜水溶性粗多糖提取及降血糖功能研究

采用热水浸提法提取苦瓜水溶性多糖.通过正交试验优选浸提条件,确定苦瓜水溶性多糖最佳提取工艺条件为:即提取温度90℃,提取水料比为30:1,提取时间2 h.对苦瓜水溶性粗多糖的降血糖活性进行研究,结果表明:苦瓜水溶性多糖能够明显降低糖尿病小鼠的血糖,刘量500 mg/kg时,效果超出甲糖宁.     

大孔吸附树脂对苦瓜皂甙的吸附研究

试验通过静态吸附对几种树脂进行筛选,结果表明D-101对苦瓜皂甙有较大的吸附率和解吸率,适合用来提取纯化苦瓜皂甙.进一步对D-101进行动态吸附研究,结果表明,浓度为95%的乙醇,3个柱体积可以洗脱几乎所有的苦瓜皂甙.苦瓜皂甙粗提物的上样浓度为2.8～5.6 ms/mL之间.     

A lanostane aldehyde from Momordica charantia

A new lanostane aldehyde, charantal (1), was isolated from the ethanolic leaf extract of Momordica charantia together with the known compound, 2,4-bis(2-phenylpropan-2-yl)phenol (2). The structure of compound 1 was elucidated by extensive 1D and 2D NMR and MS experiments. Compound 2 displayed a moderately strong antitubercular activity against Mycobacterium tuberculosis H₃₇Rv (MIC = 14 μg/mL) according to the MABA susceptibility assay.     

New labdane diterpenes from the aerial parts of Scoparia dulcis L.

Three new labdane-derived diterpenes, dulcinodal (1), dulcinodiol (2), and scopadiol decanoate (3) were isolated from the aerial parts of Scoparia dulcis. The structures were determined by extensive NMR studies and comparison of their spectral data with related compounds.